1,2-Dichloroethane → (+/-)-3'-Methyl-2',5'-dioxo-N-phenyl-6,8-dihydrospiro[cyclopenta[g]quinoline-7,4'-imidazolidine]-2-carboxamide

HRID 656376Notes

Reaction equation

HRID 656376 reaction equation
[CH3:1][N:2]1[C:6]2([CH2:21][C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][C:8]=3[CH2:7]2)[N:15]=[C:14]([C:18](O)=[O:19])[CH:13]=[CH:12]4)[C:5](=[O:22])[NH:4][C:3]1=[O:23].[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:1][N:2]1[C:6]2([CH2:21][C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][C:8]=3[CH2:7]2)[N:15]=[C:14]([C:18]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:19])[CH:13]=[CH:12]4)[C:5](=[O:22])[NH:4][C:3]1=[O:23]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57774222(+/-)-3'-Methyl-2',5'-dioxo-6,8-dihydrospiro[cyclopenta[g]quinoline-7,4'-imidazolidine]-2-carboxylic acid2×

Product 1

HCID 23627804(+/-)-3'-Methyl-2',5'-dioxo-N-phenyl-6,8-dihydrospiro[cyclopenta[g]quinoline-7,4'-imidazolidine]-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (±)-3′-methyl-2′,5′-dioxo-6,8-dihydrospiro[cyclopenta[g]quinoline-7,4′-imidazolidine]-2-carboxylic acid (14 mg, 0.045 mmol, described in Intermediate 18), aniline (4 mg, 0.045 mmol), EDC (26 mg, 0.136 mmol), HOBT (21 mg, 0.136 mmol), and N,N-diisopropylethylamine (0.039 mL, 0.226 mmol) is stirred in DMF (1 mL) at ambient temperature for 18 h. The reaction mixture is purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. The pure, product-containing fractions are combined and concentrated to give the title compound.

Workup

  1. customThe reaction mixture is purified directly by HPLC
  2. washeluting with a gradient of H2O
  3. additionThe pure, product-containing fractions
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ab040129ec514a41a8384e620fb6e4fd
Source dataset
uspto-grants-2011_12
Patent number
US08071770B2

Reaction notes

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